HCID 70485509, compound → HCID 70485452, compound

Participants

Reaction Steps

A solution of N-(tert-butyloxycarbonyl)-O-(tert-butyl)-L-tyrosyl-N-[3-(methylthio)propyl]-N-(3-phenylpropyl)-D-alaninamide (2.42 g.) in hydrogen chloride-dioxane (3.9N, 50 ml.) was stirred for one and one half hours at room temperature, then stripped of volatiles under vacuum. The residue was triturated with ether, the solution was stripped of volatiles under vacuum, and the process was repeated. An aqueous solution of the residue was lyophilized. A solution of the residue in methanol (50 ml.) was stripped of volatiles, affording a white foam (1.960 g.). Part (950 mg.) of the white foam was twice more lyophilized, affording as an amorphous white solid L-tyrosyl-N-[3-(methylthio)propyl]-N-(3-phenylpropyl)-D-alaninamide monhydrochloride hemihydrate (675 mg.; [α]D25 +57.0, c=1, methanol), whose free base is the compound of Formula II wherein R2 is CHQ(CH2)nY wherein n is 2, Y is phenyl and Q is hydrogen and R3 is (CH2)mX wherein m is 3 and X is methylthio.

Provenance & Evidence